cis-1,2,3,3a,4,9b-hexahydro-cyclopenta[a]naphthalen-5-one | 35444-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: cis-1,2,3,3a,4,9b-hexahydro-cyclopenta[a]naphthalen-5-one
• 英文别名: (+/-)-5-oxo-cis-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalene；(+/-)-5-Oxo-cis-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalin；(3aR,9bR)-1,2,3,3a,4,9b-hexahydrocyclopenta[a]naphthalen-5-one
• CAS: 35444-86-1；111386-42-6
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: UXJPIIGTIKJHNM-NXEZZACHSA-N

物化性质

• 沸点：
  190-192 °C(Press: 20 Torr)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-1,2,3,3a,4,9b-hexahydro-cyclopenta[a]naphthalen-5-one 在 过氧化氢异丙苯 、 C₅₃H₆₅F₁₂N₇O₂*ClH 、 sodium hydride 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 3-苯基-2-甲苯磺酰-1,2-氧杂氮杂环丙烷 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  Oxidative Kinetic Resolution of cis-Fused Tricyclic 1-Tetralone Derivatives by Guanidine–Bisurea Bifunctional Organocatalyst

  摘要：

  我们提出了一种手性选择性合成顺式融合的三环1-四酮，该合成方法采用叔丁基过氧化氢（CHP）和胍-双脲双官能团有机催化剂存在下的氧化动力学分辨法。该反应以良好至高手性选择性的形式提供了相应的α-羟基化产物以及未反应的四酮，s值高达42。该反应成功地应用于合成kainoid衍生物的核心结构，即4-(2-甲氧基苯基)-2-羧基-3-吡咯烷乙酸（MFPA）。

  DOI：

  10.1055/s-0036-1588151
• 作为产物：
  描述：

  (1S,5S)-5-phenylbicyclo[3.2.0]heptan-6-one 在 氢氟酸 、 potassium ethoxide 、 水 作用下， 反应 3.0h， 生成 cis-1,2,3,3a,4,9b-hexahydro-cyclopenta[a]naphthalen-5-one
  参考文献：
  名称：

  芳基烯酮与烯烃的分子内环加成：5-芳基双环[3.2.0]庚烷-6-酮的反应

  摘要：

  芳基烯酮4的分子内环加成反应以优异的收率进行，得到5 -arylbicy-clo [3.2.0] heptan-6-ones 5。的反应图5a与KOH在THF给出了一个95：5混合物7和10。5a与KOEt在ETOH中的反应得到1：3的7和10的混合物。5a与乙烯基锂的反应以及用KH处理所得的醇23得到1，3-σ重排产物25。

  DOI：

  10.1016/0040-4039(88)85114-1

文献信息

• CO-Trapping Reaction under Thermolysis of Alkoxyamines:  Application to the Synthesis of 3,4-Cyclopenta-1-tetralones
  作者：Yoshitaka Uenoyama、Masaaki Tsukida、Takashi Doi、Ilhyong Ryu、Armido Studer

  DOI：10.1021/ol050951n

  日期：2005.7.1

  An efficient one-pot sequence comprising a PRE-mediated radical 5-exo-cyclization, a radical carbonylation, a nitroxide trapping reaction, and a subsequent acid-catalyzed Friedel-Craft-type acylation provides a new entry into 3,4-cyclopenta-1-tetral ones. Eight examples are presented.
• Drug interaction studies between paclitaxel (Taxol) and OC144-093 — A new modulator of MDR in cancer chemotherapy
  作者：Emma S. Guns、Tetyana Denyssevych、Ross Dixon、Marcel B. Bally、Lawrence Mayer

  DOI：10.1007/bf03190426

  日期：2002.6

  The MDR modulator, OC144-093, is a potential candidate for use in cancer therapy and exhibits potent biological activity in vitro and in vivo when combined with anticancer agents such as paclitaxel [1]. Its inhibitory interaction with P-glycoprotein (Pgp), the mdr1 gene product and a mechanistic participant in multidrug resistance[2], underlies its activity as a modulator of MDR. Having previously shown that OC144-093 is not a substrate for CYP3A [4] we first examined the effects of OC144-093 on paclitaxel metabolism in vitro. Using human liver microsomes, we have demonstrated that OC144-093 inhibited the CYP3A mediated metabolism of paclitaxel at high concentrations only (Ki = 39.8+/-5.1 muM, n=3). Pharmacokinetic results also show that an oral dose of OC144-093, co-administered with paclitaxel caused negligible disturbance of the pharmacokinetic profile for paclitaxel when injected intravenously. In contrast, AUC values were elevated approximately 1.5-fold in all groups treated orally with paclitaxel and OC144-093. Cmax was enhanced approximately 2-fold in the co-dosed group. These characteristics are consistent with Pgp blockade in the gut enhancing oral bioavailability. Elimination proper-ties of paclitaxel were affected only upon multiple dosing of OC144-093. These results warrant the further clinical assessment of OC144-093 as an MDR reversing agent.
• SNIDER, BARRY B.;NIWA, MAHO, TETRAHEDRON LETT., 29,(1988) N 26, C. 3175-3178
  作者：SNIDER, BARRY B.、NIWA, MAHO

  DOI：——

  日期：——